CA2169719A1 - Pyrazolo[1,5-a]pyrimidine derivative - Google Patents

Pyrazolo[1,5-a]pyrimidine derivative

Info

Publication number
CA2169719A1
CA2169719A1 CA002169719A CA2169719A CA2169719A1 CA 2169719 A1 CA2169719 A1 CA 2169719A1 CA 002169719 A CA002169719 A CA 002169719A CA 2169719 A CA2169719 A CA 2169719A CA 2169719 A1 CA2169719 A1 CA 2169719A1
Authority
CA
Canada
Prior art keywords
lower alkyl
phenyl
represents hydrogen
pyrazolo
pyrimidine derivative
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002169719A
Other languages
French (fr)
Other versions
CA2169719C (en
Inventor
Yasuo Shoji
Tsuneo Yasuda
Makoto Inoue
Takashi Okamura
Kinji Hashimoto
Masayuki Ohara
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Otsuka Pharmaceutical Factory Inc
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2169719A1 publication Critical patent/CA2169719A1/en
Application granted granted Critical
Publication of CA2169719C publication Critical patent/CA2169719C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

A pyrazolo[1,5-a]pyrimidine derivative represented by general formula (1) and having such a potent analgesic effect that it is useful as an analgesic, wherein R1 represents hydrogen, lower alkyl, cycloalkyl, thienyl, furyl, lower alkenyl or phenyl; R2 represents naphthyl, cycloalkyl, furyl, thienyl, pyridyl, phenoxy or phenyl; R3 represents hydrogen, phenyl or lower alkyl; R4 represents hydrogen, lower alkyl, lower alkoxy-carbonyl, phenyl-substituted lower alkyl, phenyl or halogen; R5 represents hydrogen or lower alkyl; R6 represents hydrogen, lower alkyl, phenyl-substituted lower alkyl or benzoyl; Q
represents carbonyl or sulfonyl; A represents a single bond, lower alkylene or lower alkenylene; and n represents 0 or 1.
CA002169719A 1994-06-21 1995-06-05 Pyrazolo[1,5-a]pyrimidine derivative Expired - Fee Related CA2169719C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
JP13863594 1994-06-21
JP6/138635 1994-06-21
JP5399795 1995-03-14
JP7/53997 1995-03-14
PCT/JP1995/001104 WO1995035298A1 (en) 1994-06-21 1995-06-05 PYRAZOLO[1,5-a]PYRIMIDINE DERIVATIVE

Publications (2)

Publication Number Publication Date
CA2169719A1 true CA2169719A1 (en) 1995-12-28
CA2169719C CA2169719C (en) 2002-04-16

Family

ID=26394734

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002169719A Expired - Fee Related CA2169719C (en) 1994-06-21 1995-06-05 Pyrazolo[1,5-a]pyrimidine derivative

Country Status (13)

Country Link
US (1) US5707997A (en)
EP (1) EP0714898B1 (en)
KR (1) KR100315837B1 (en)
CN (1) CN1046730C (en)
AT (1) ATE208776T1 (en)
AU (1) AU680370B2 (en)
CA (1) CA2169719C (en)
DE (1) DE69523864T2 (en)
DK (1) DK0714898T3 (en)
ES (1) ES2164153T3 (en)
PT (1) PT714898E (en)
TW (1) TW307767B (en)
WO (1) WO1995035298A1 (en)

Families Citing this family (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0795555A4 (en) * 1995-09-28 1998-01-07 Otsuka Pharma Co Ltd Analgesics
US6664261B2 (en) * 1996-02-07 2003-12-16 Neurocrine Biosciences, Inc. Pyrazolopyrimidines as CRF receptor antagonists
US6313124B1 (en) 1997-07-23 2001-11-06 Dupont Pharmaceuticals Company Tetrazine bicyclic compounds
US6060478A (en) * 1996-07-24 2000-05-09 Dupont Pharmaceuticals Azolo triazines and pyrimidines
US6124289A (en) * 1996-07-24 2000-09-26 Dupont Pharmaceuticals Co. Azolo triazines and pyrimidines
DK0915880T3 (en) * 1996-07-24 2008-02-11 Bristol Myers Squibb Pharma Co Azolotriazines and pyrimidines
US7094782B1 (en) 1996-07-24 2006-08-22 Bristol-Myers Squibb Company Azolo triazines and pyrimidines
US6191131B1 (en) 1997-07-23 2001-02-20 Dupont Pharmaceuticals Company Azolo triazines and pyrimidines
TW495509B (en) * 1997-03-14 2002-07-21 Otsuka Pharma Co Ltd Novel pyrimidine derivative
CA2359041A1 (en) * 1999-01-29 2000-08-03 Sumitomo Chemical Co., Ltd. Fat accumulation inhibitory agents
WO2000059908A2 (en) 1999-04-06 2000-10-12 Du Pont Pharmaceuticals Company Pyrazolopyrimidines as crf antagonists
WO2000059907A2 (en) 1999-04-06 2000-10-12 Du Pont Pharmaceuticals Company Pyrazolotriazines as crf antagonists
US20020061897A1 (en) 2000-03-30 2002-05-23 Elliott Richard L. Neuropeptide Y antagonists
US6630476B2 (en) 2000-07-07 2003-10-07 Bristol-Myers Squibb Pharma Company Pyrrolo [3,4-d] pyrimidines as corticotropin releasing factor (CRF) antagonists
SE0102764D0 (en) 2001-08-17 2001-08-17 Astrazeneca Ab Compounds
CA2465326C (en) * 2001-11-01 2011-03-29 Icagen, Inc. Pyrazolopyrimidines for decreasing ion flow through a voltage-dependent sodium channel
US20040028716A1 (en) * 2002-06-14 2004-02-12 Marks Andrew R. Use of Y-27632 as an agent to prevent restenosis after coronary artery angioplasty/stent implantation
CA2497539A1 (en) 2002-09-04 2004-03-18 Schering Corporation Novel pyrazolopyrimidines as cyclin dependent kinase inhibitors
US7161003B1 (en) * 2002-09-04 2007-01-09 Schering Corporation Pyrazolopyrimidines as cyclin dependent kinase inhibitors
US7119200B2 (en) 2002-09-04 2006-10-10 Schering Corporation Pyrazolopyrimidines as cyclin dependent kinase inhibitors
US8673924B2 (en) 2002-09-04 2014-03-18 Merck Sharp & Dohme Corp. Substituted pyrazolo[1,5-a]pyrimidines as cyclin dependent kinase inhibitors
US8580782B2 (en) 2002-09-04 2013-11-12 Merck Sharp & Dohme Corp. Substituted pyrazolo[1,5-a]pyrimidines as cyclin dependent kinase inhibitors
US7205308B2 (en) * 2002-09-04 2007-04-17 Schering Corporation Trisubstituted 7-aminopyrazolopyrimidines as cyclin dependent kinase inhibitors
US7196078B2 (en) * 2002-09-04 2007-03-27 Schering Corpoartion Trisubstituted and tetrasubstituted pyrazolopyrimidines as cyclin dependent kinase inhibitors
TW200413377A (en) * 2002-09-04 2004-08-01 Schering Corp Novel pyrazolopyrimidines as cyclin dependent kinase inhibitors
TWI344468B (en) 2002-09-04 2011-07-01 Schering Corp Novel pyrazolopyrimidines as cyclin dependent kinase inhibitors
CA2497450C (en) 2002-09-04 2011-05-31 Schering Corporation Pyrazolopyrimidines as cyclin dependent kinase inhibitors
AU2003298571B2 (en) * 2002-09-04 2006-10-19 Merck Sharp & Dohme Corp. Pyrazolo[1,5-a]pyrimidines compounds as cyclin dependent kinase inhibitors
US6949895B2 (en) * 2003-09-03 2005-09-27 Axcelis Technologies, Inc. Unipolar electrostatic quadrupole lens and switching methods for charged beam transport
AR049769A1 (en) * 2004-01-22 2006-09-06 Novartis Ag DERIVATIVES OF PIRAZOLO (1,5-A) PIRIMIDIN 7-IL-AMINA TO BE USED IN THE TREATMENT OF DEPENDENT DISEASES OF PROTEIN KINASE
WO2006040645A1 (en) * 2004-10-11 2006-04-20 Ranbaxy Laboratories Limited N-(3,5-dichloropyridin-4-yl)-2,4,5-alkoxy and 2,3,4-alkoxy benzamide derivatives as pde-iv (phophodiesterase type-iv) inhibitors for the treatment of inflammatory diseases such as asthma
GB0519957D0 (en) 2005-09-30 2005-11-09 Sb Pharmco Inc Chemical compound
TW200639163A (en) 2005-02-04 2006-11-16 Genentech Inc RAF inhibitor compounds and methods
WO2006092412A1 (en) * 2005-03-01 2006-09-08 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-azolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
TW200643022A (en) * 2005-03-02 2006-12-16 Basf Ag 2-substituted 7-aminoazolopyrimidines, processes for their preparation and their use for controlling harmful fungi, and compositions comprising these compounds
JP2009507843A (en) * 2005-09-09 2009-02-26 シェーリング コーポレイション Aza-fused cyclin-dependent kinase inhibitors
KR20080063806A (en) 2005-10-06 2008-07-07 쉐링 코포레이션 Pyrazolopyrimidines as protein kinase inhibitors
MX2009005478A (en) * 2006-11-27 2009-08-12 Lundbeck & Co As H Heteroaryl amide derivatives.
EP2155744A1 (en) * 2007-04-10 2010-02-24 Lundbeck, H., A/S Heteroaryl amide analogues as p2x7 antagonists
AR076221A1 (en) 2009-04-09 2011-05-26 Astrazeneca Ab DERIVED FROM PIRAZOL [4,5-E] PYRIMIDINE AND ITS USE TO TREAT DIABETES AND OBESITY
JP6073343B2 (en) 2011-10-20 2017-02-01 グラクソスミスクライン・リミテッド・ライアビリティ・カンパニーＧｌａｘｏＳｍｉｔｈＫｌｉｎｅ ＬＬＣ Substituted bicyclic azaheterocycles and analogs as sirtuin regulators
CN103998451A (en) * 2011-10-20 2014-08-20 葛兰素史密斯克莱有限责任公司 Substituted bicyclic aza-heterocycles and analogues as sirtuin modulators
AR085073A1 (en) * 2012-01-11 2013-09-11 Richmond Sa Com Ind Y Financiera Lab COMPOUNDS WITH ANTIBACTERIAL ACTIVITY, A PROCEDURE FOR OBTAINING AND PHARMACEUTICAL COMPOSITIONS THAT UNDERSTAND THEM
AU2014372638A1 (en) 2013-12-23 2016-06-16 Norgine B.V. Compounds useful as CCR9 modulators
US20170002011A1 (en) * 2013-12-23 2017-01-05 Norgine B.V. Benzene sulfonamides as ccr9 inhibitors
WO2015143652A1 (en) * 2014-03-26 2015-10-01 Merck Sharp & Dohme Corp. TrkA KINASE INHIBITORS,COMPOSITIONS AND METHODS THEREOF
EP3873911A4 (en) * 2018-10-30 2022-06-22 Kronos Bio, Inc. Compounds, compositions, and methods for modulating cdk9 activity

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3925385A (en) * 1972-04-20 1975-12-09 Icn Pharmaceuticals 6-Carbethoxy-3,7-disubstitutedpyrazolo{8 1,5a{9 pyrimidines
BE792533A (en) * 1971-12-09 1973-06-08 Int Chem & Nuclear Corp NEW PYRAZOLO (1.5A) PYRIMIDINES AND THEIR PREPARATION PROCESS
JPS6157587A (en) * 1984-08-29 1986-03-24 Shionogi & Co Ltd Condensed heterocyclic derivative and antiulcerative
US4950585A (en) * 1987-08-18 1990-08-21 Konica Corporation Coupler for photographic use
JP2585462B2 (en) * 1989-10-25 1997-02-26 株式会社大塚製薬工場 Pyrazolo [1,5-a] pyrimidine derivatives
EP0591528B1 (en) * 1991-04-22 1998-12-23 Otsuka Pharmaceutical Factory, Inc. PYRAZOLO[1,5-a]PYRIMIDINE DERIVATIVE AND ANTI-INFLAMMATORY CONTAINING THE SAME
KR0133372B1 (en) * 1991-09-06 1998-04-23 고야 다다시 4-amino (alkyl) cyclohexane-1-carboxamide compound and use
US5571813A (en) * 1993-06-10 1996-11-05 Beiersdorf-Lilly Gmbh Fused pyrimidine compounds and their use as pharmaceuticals

Also Published As

Publication number Publication date
AU2576595A (en) 1996-01-15
WO1995035298A1 (en) 1995-12-28
EP0714898A4 (en) 1997-04-02
EP0714898A1 (en) 1996-06-05
DK0714898T3 (en) 2002-03-18
DE69523864D1 (en) 2001-12-20
CA2169719C (en) 2002-04-16
DE69523864T2 (en) 2002-06-13
ATE208776T1 (en) 2001-11-15
KR960703919A (en) 1996-08-31
US5707997A (en) 1998-01-13
ES2164153T3 (en) 2002-02-16
CN1131948A (en) 1996-09-25
TW307767B (en) 1997-06-11
AU680370B2 (en) 1997-07-24
CN1046730C (en) 1999-11-24
PT714898E (en) 2002-04-29
KR100315837B1 (en) 2002-02-28
EP0714898B1 (en) 2001-11-14

Similar Documents

Publication Publication Date Title
CA2169719A1 (en) Pyrazolo[1,5-a]pyrimidine derivative
CA2173150A1 (en) Novel peptide derivatives
CA2302445A1 (en) New taxane derivatives
AU2267195A (en) Dc-89 derivative
IE892438L (en) Aminomethyloxooxazolidinyl Arylbenzene derivatives useful¹as Antibacterial agents
CA2275635A1 (en) Pesticidal 1-arylpyrazoles
CA2028163A1 (en) Solid antimicrobial
AU6198990A (en) Platinum catalyzed heterocyclic compound compositions
CA2103836A1 (en) 7-(substituted)-9-[(substituted glycyl)-amido]-6-demethyl-6-deoxytetracyclines
AU8979191A (en) 3,7-disubstituted indole derivatives
CA2219675A1 (en) Pentacyclic compound
AU7855191A (en) 2',3'-dideoxy-4'-thioribonucleosides as antiviral agents
CA2082923A1 (en) Sulfonyl compounds
CA2138289A1 (en) N-substituted azabicycloheptane derivatives, the preparation and use thereof
BG98124A (en) Active pyrrole-(2,3-)pyridine derivatives
AU8163091A (en) Novel tricyclic compound or salts thereof, method for producing the same and antimicrobial agent containing the same
AU7930691A (en) An aqueous tiecoat composition
AU5161593A (en) Heterocyclic compound
EP0822194A4 (en) FUSED IMIDAZO 1,2-a]PYRIDINES
AU575342B2 (en) Gamma - butyrolactone derivatives
EP0754683A4 (en) Ether compound, use thereof, and intermediate for producing the compound
AU7809991A (en) Pharmacologically active cns compounds
CA2182477A1 (en) Pyridyl Imidazole Derivatives and Processes for the Preparation Thereof
AU1303099A (en) Herbicidal furanyl- and thienyloxyazines
AU8542991A (en) Heterocyclic compounds

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed